Acetic Acid → HCID 59204536, compound

HRID 1096548Notes

Reaction equation

HRID 1096548 reaction equation
[S:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([CH:10]=O)=[C:4]2[N:3]=[CH:2]1.[CH2:12]([O:14][CH:15]([O:18][CH2:19][CH3:20])[CH2:16][NH2:17])[CH3:13].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][NH:17][CH2:16][CH:15]([O:18][CH2:19][CH3:20])[O:14][CH2:12][CH3:13])[C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 695242,2-DiethoxyethylamineHCID 5003444Sodium cyanoborohydrideHCID 717000301,3-Benzothiazole-4-carbaldehyde

Product 1

HCID 59204536HCID 59204536, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Benzothiazole-4-carbaldehyde (1.96 g, 12 mmol) in MeOH (50 mL) was added aminoacetaldehyde diethyl acetal (1.74 mL, 12 mmol) and acetic acid (1.03 mL, 18 mmol). The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was added to a stirred solution of sodium cyanoborohydride (816 mg, 13 mmol). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was concentrated under reduced pressure. Then H2O and ethyl acetate were added to the reaction mixture. The organic layer was washed with H2O and brine, dried over Na2SO4, and concentrated under reduced pressure. The crude compound was used next step without further purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 12 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThen H2O and ethyl acetate were added to the reaction mixture
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customwithout further purification

Sources & evidence

ORD record
ord-c8c2ada9101e4308bb6f218132e20007
Source dataset
uspto-grants-2012_03
Patent number
US08138337B2

Reaction notes

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